Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B53/00—Quinone imides
  • C09B53/02—Indamines; Indophenols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/413—Indoanilines; Indophenol; Indoamines
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/01—Aerosol hair preparation
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/02—Resin hair settings

Definitions

• a dye composition for keratinous fibers and in particular, human hair comprises an aqueous solution of an indoaniline having the formula wherein R R R and R each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-6 carbon atoms and halogen with the proviso that 1 2 of R R R and R are other than hydrogen; R R and R each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 16 carbon atoms and lower .alkoxy having 1-6 carbon atoms; R represents a member selected from the group consisting of hydrogen and lower alkyl having 1-6 carbon atoms; R represents a member selected from the group consisting of hydrogen and lower alkyl having 16 carbon atoms and together with R and the nitrogen atom to which R is attached form dihydrooxazine; and Z represents a member
• R R R and R each independently represents a member selected from the group consisting of hydrogen, lower alkyl having 1 6 carbon atoms and halogen such as chlorine and bromine with the proviso that l 2 of R R R and R are other than hydrogen;
• R R and R each independently represent a member selected from the group consisting of lower alkyl having 1 6 carbon atoms and lower alkoxy having 1 6 carbon atoms;
• R represents a member selected from the group consisting of hydrogen, lower alkyl having I 6 carbon atoms, lower alkyl having I 6 carbon atoms and substituted with a member selected from the group consisting of amino, hydroxyl, carbamoyl, piperidinyl and acylamino and together with R and the nitrogen atom to which R is attached form a heterocycle selected from the group consisting of
• the organic or inorganic acid salts of the compounds of formula l can be acetates, oxalates, hydrochlorides, hydrobromides, persulfates or perchlorates.
• indoanilines or indoaniline salts of formula I can be prepared by four different processes described below.
• Method 1 A first process of obtaining the indoanilines of formula l or their salts comprises reacting a paraaminophenol having the formula:
• the reaction can be performed in an aqueous medium, an aqueous alcoholic medium or an aqueous acetonic medium, at a pH made alkaline by addition to said chosen medium of an aqueous solution of sodium, potassium or ammonium hydroxide, the pH preferably ranging from about 8 to 10 at a temperature between 5C and 40C and in the presence of an oxidizing agent such as air, hydrogen peroxide, ammonium persulfate or potassium ferricyanide.
• the indoaniline of formula I is then isolated in the form of a free base.
• an aqueous alcoholic medium the alcohol can be present in amounts of about 20 to 50 percent by weight of said medium and the alcohol employed is generally a lower alkanol having 1 4 carbon atoms.
• ac etone can comprise between about l0 to 30 weight percent of the medium.
• the amount of oxidizing agent used can vary be tween about one to five times the stoichiometric quantity for oxidizing the paraaminophenol to the corresponding quinone-imine. This amount is preferably 1-3 moles of persulphate or 2-5 moles of ferricyanide for 1 mole of paraaminophenol.
• the reaction can also be performed in an aqueous medium between 0 and 20C at an acid pH, preferably ranging from about 1 to 5, and in the presence of a ferric chloride solution present in amounts of about 2 to 6 moles per mole of paraaminophenol.
• a ferric chloride solution present in amounts of about 2 to 6 moles per mole of paraaminophenol.
• the indoaniline of formula I is then isolated in the hydrochloride form.
• paraaminophenols of formula II that can be used in accordance with the present invention are, 3-methyl-4-amino phenol, 7.,5-dimethyl-4-amino phenol, 3,5-dimethyl-4-amino phenol, 2,3-dimethyl-4- amino phenol, 2-rnethyl-4-amino phenol, 2,6-dimethyl- 4-amino phenol, 2,6-di-tert -butyl-4-amino phenol, 2- chloro-4-amino phenol and 3-cchloro-4amino phenol.
• Compounds representative of those of formula lll include metaphenylenediamine, metatoluylenediamine, 2,4-diamino anisole, 3,5-diamino toluene, 1,3- dimethyl-2,4-diamino benzene, N,N-dimethyl metaphenylenediamine, 6-hydroxy phenomorpholine, 6- hydroxy-4-methyl phenomorpholine, 3-acetylamino N,N-dimethylaniline, 2-methyl-5-acetylaminoaniline, 6-amino phenomorpholine, and l-ethyl-6-amino indoline.
• paraaminophenol represented by formula II and the compound represented by formula III are employed in essentially equirnolar amounts.
• the indoanilines of formula I can also be prepared by condensation of a benzoquinenemonoimine having formula cm (v) wherein R R R and R have the meaning given above, on compound of formula [I], this condensation being performed in an aqueous medium, an aqueous alcoholic medium or an aqueous acetonic medium, also as defined above, at a temperature between and 40C.
• quinone-chloroimides that can be used include, for example, 3-methyl quinone chloroimide, 2-chloro quinone chloroimide, 3-chloro quinone chloroimide, 2,5-dimethyl quinone chloroimide, 2,3- dimethyl quinone chloroimide and 3,5-dimethy] quinone chloroimide.
• Essentially equimolar amounts of the quinone-chloroimide and compound III are employed.
• the indoanilines of formula lean also be prepared by reacting a nitroso derivative having the formula OH- --OH wherein R R R and R, have the meaning above, with a compound of formula Ill.
• the condensation reaction is performed in an alcohol medium in the presence of zinc chloride at the reflux temperature of the reaction medium.
• the indoaniline is then isolated in the form of double zinc salt.
• the alcohol used for the reaction medium can be a lower alkanol having l 4 carbon atoms and the zinc chloride is generally present in amounts sufficient for precipitating the product.
• the indoanilines according to the present invention and their salts constitute dyes which present good dyeing power with regard to keratinous fibers and, in particular, human hair, this in a pH range varying from 4 to 11. Because of their great affinity for these fibers they can be used at very slight concentrations, for instance, from about 0.002 to 0.005% by weight of the dye composition, which explains why even salts that are only slightly soluble in water can be effectively used.
• indoanilines of the present invention make it possible to obtain a very wide range of shades, in particular violets, blues, greens, roses, silver grays and ash blonds which present exceptional qualities of brilliance and richness in glints. After dyeing, the hair presents a pearly and iridescent appearance.
• the present invention also provides a novel dying composition for keratinous fibers, in particular human hair, characterized by the fact that it contains in solution at least a compound of formula I or a salt of this compound.
• the dye compositions according to the invention can contain only the compounds of formula I, in which case they make it possible to obtain the entire range of shades, with the exception of the yellows, and with application times that can be extremely short, of the order of 3 minutes at ambient temperature, because of the great affinity of the indoanilines of formula I with regard to keratinous fibers.
• compositions according to the invention can also contain other direct dyes, for example, anthraquinone dyes, nitro dyes of the benzene series, indamines, indophenols, oxazines, azines or indoanilines other than those of formula l.
• direct dyes for example, anthraquinone dyes, nitro dyes of the benzene series, indamines, indophenols, oxazines, azines or indoanilines other than those of formula l.
• compositions according to the invention can, as has been said above, be extremely slight, of the order of 0.002% by weight. However, this concentration can vary from 0.002 to 2% and preferably between about 0.005 and 0.5% by weight.
• the dye compositions according to the present invention are in the form of aqueous solutions, to which most often have been added low molecular weight alcohols such as ethanol or isopropanol, or glycols such as propyleneglycol or butyglycol, the alcohol or glycol facilitating the solution of the dye in the composition.
• alcohols such as ethanol or isopropanol
• glycols such as propyleneglycol or butyglycol
• the proportion of alcohol used is generally between 20 and by weight, while the proportion of glycol is generally between 1 and 6% by weight.
• compositions according to the invention can also contain various ingredients usually used in capillary cosmetics, for example, wetting agents, dispersing agents, swelling agents, penetrating agents, thickeners, softeners or perfumes. They can also be packaged under pressure in aerosol bombs or containers, together with a conventional aerosol propellant such as dichlorodifluoromethane, trichloromonofluoromethane and their mixtures. Obviously other conventional aerosol propellants can be used.
• a conventional aerosol propellant such as dichlorodifluoromethane, trichloromonofluoromethane and their mixtures. Obviously other conventional aerosol propellants can be used.
• the pH of the dye compositions according to the invention can vary between 4 and l l. Preferably, however, the pH ranges between 5 and 9. To regulate this pH at a desired value, it is possible to use as alkalizing agents ammonia or an amine such as monoor dior triethanolamine and as acidifying agents, acetic acid or lactic acid.
• Dyeing of keratinous fibers, in particular, human ,hair, with the dye compositions according to the invention can be performed in the usual way, by application of the composition to the fibers to be dyed, the composition being left in contact with the fibers for a time varying from 3 to 30 minutes. Following this application, the fibers are rinsed and, if desired, washed. Thereafter, the thus treated fibers are dried.
• the novel indoanilines can be employed in the production of capillary hair-setting lotions.
• These lotions comprise an aqueous alcohol solution, at least one cosmetic resin and at least one indoaniline of formula I or a salt thereof.
• the amount of indoaniline or its salt present in the hair-setting lotion according to this invention can be extremely slight. Such an amount generally varies between 0.002 and 1% by weight and preferably between 0.002 and 0.5% by weight, of the total hairsetting lotion composition, the pH of which generally lies between 5 8.
• Representative cosmetic resins that can be employed in the hair-setting lotions of the present invention include, for instance, polyvinylpyrrolidone having a molecular weight of 40,000-400,000, copolymer of crotonic acid and vinyl acetate, said copolymer having a molecular weight ranging from about 10,000 to 70,000, copolymer vinylpyrrolidone and vinyl acetate, wherein the ratio of VP to VA ranges between 50 70: 50 30, said copolymer having a molecular weight ranging from about 30,000 to 200,000 and maleic anhydride butylvinyl ether copolymers, a 1% solution of which in methylethyl ketone has a viscosity of O.13.5 cps at 25C. These resins are used in a proportion of 1 to 3% by weight of the hair-setting lotion composition.
• the alcohols suitable for the preparation of the hairsetting lotions according to the invention are low molecular weight alkanols, such as ethanol or isopropanol which are present in amounts of about to 70% by weight of the total hair-setting lotion composition.
• the setting lotion of the present invention can contain only the indoanilines of formula 1, in which case they constitute shading compositions which make it possible to give the hair extremely luminous glints and a pearly or iridescent appearance.
• the hair-setting lotions of this invention can also contain other direct dyes, for example, anthraquinone dyes, nitro dyes of the benzene series, indamines, indophenols, oxazines, azines or indoanilines other than those of formula I.
• direct dyes for example, anthraquinone dyes, nitro dyes of the benzene series, indamines, indophenols, oxazines, azines or indoanilines other than those of formula I.
• the hair-setting lotions according to the invention are usually used by application to wet hair, previously washed and rinsed, followed by rolling the hair up on curlers and drying the hair.
• N-[(2',4-diamino3',5'-dimethyl) phenyl]-3-methyl benzoquinone imine is prepared as follows CH3 NHQ CH3
• the two solutions, previously cooled, are mixed and the reaction mixture is allowed to stand for 20 minutes at 0C.
• the above indoaniline precipitates in the form of green crystals with golden glints. It is filtered, washed with ethyl alcohol and then with water. After vacuum drying, the product is chromatographically pure and melts at C.
• dimethyl benzoquinone imine is prepared in accordance with method 2 as follows:
• a solution is prepared by dissolving 0.02 mole (3.60 g) of 2chloro-4-amino phenol hydrochloride in 50 cc of water. To this solution, cooled in an ice bath, there are added simultaneously, with stirring, with the aid of two dropping funnels, on the one hand, 0.02 mole (4.22 g) of 2,4-diamino anisole dihydrochloride dissolved in 50 cc of water, and, on the other hand, 0.02 mole (4.60 g) of ammonium persulfate dissolved in 50 cc of ice water to which have been added 50 cc of ammonia at 22 Be. The reaction mixture is allowed to stand for 15 minutes at 0C. The above indoaniline precipitates in crystallized form and is filtered therefrom. after which it is washed with water and vacuum dried. The product is chromatographically pure and melts at 197C.
• chloro benzoquinone imine having the below formula, is prepared as follows:
• Step 2 There are dissolved 0.003 mole (0.627 g) of 1,3- dimethyl-2,4-diamino benzene dihydrochloride in 10 cc of water to which has been added 1 cc of ammonia at 22 Be. To this solution, cooled in ice, there is added 0.002 mole (0.27 g) of the above 2,3-dimethyl benzoquinone monomine, dissolved at the moment of use in 5 cc of isopropanol. The above indoaniline, which precipitates, is filtered, washed with water and vacuum dried. The indoaniline melts at 206C and does not show any drop in its melting point when mixed with the product prepared according to Example 4.
• EXAMPLE 17 The double chloride of zinc and N-[7'-(6-hydroxy- 4'-methyl-l '-oxa-4'-aza-1,2',3 ',4'-tetrahydro)-naph- Into cc of absolute ethyl alcohol there are introduced 0.01 mole (1.65 g) of 6-hydroxy-4-methyl phenomorpholine, 0.01 mole (1.51 g) of 2,5-dimethyl paranitrosophenol and 1.5 g of anhydrous zinc chloride. The reaction mixture is heated 45 minutes with reflux, with stirring. The reaction mass is then filtered hot to eliminate an insoluble light material. After cooling, 2.10 g of the double chloride of zinc and indoaniline are filtered which, after washing with alcohol and ethyl acetate, is chromatographically pure.
• N-[(2,4-diamino-6'-methyl) phenyl]-2,6-dimethyl benzoquinoneimine having the below formula, is prepared as follows:
• N-[(2',4'-diamino-5'-methyl) phenyl]-2,6-dimethyl benzoquinoneimine having the below formula, is prepared as follows:
• the crude product is filtered, washed with water and then with iced acetone to eliminate traces of N-[(4-hydroxy-3,5-dimethyl) phenyl]-2,6- dimethyl benzoquinoneimine. After recrystallization in a pyridine-water mixture and vacuum drying, the product melts at 240.
• mula is prepared in accordance with method 2 as follOWSI 3 2 0.003 mole (0.627 g) of l,3-dimethyl-2,4-diamino benzene dihydrochloride is dissolved in ll cc of 0.82 N soda solution. To this solution, cooled to there is added 0.002 mole (0.339 g) of 2,6-dimethyl-N- chlorobenzoquinone monoimine in solution in 6 cc of isopropanol. The reaction mixture rapidly turns blue. It is allowed to stand for one hour at 0. Then 0.400 g of the above indoaniline is isolated in the form of beautiful green flakes with golden glints by filtering. After washing with water and extended vacuum drying, the product melts at 196 (no drop of melting point is observed when used in mixture with the product prepared according to Example 22).
• This dye composition when applied for 20 minutes, at ambient temperature, to white hair, imparts thereto, after rinsing and shampooing, a mauve shade.
• Dye of Example 3 0.4 g Ethyl alcohol, 96 titer 40 g Water, q.s.p. 100 g l% lactic acid, q.s.p. pH 5 This dye composition when applied to 95% naturally white hair for 20 minutes at ambient temperature, imparts thereto after rinsing and shampooing an ash beige color with violet glints.
• EXAMPLE 38 The following hair-setting lotion composition is prepared:
• Triethanolarnine q.s.p. pH 7 This hair-setting lotion when applied to bleached hair, imparts thereto a silvery gray shade with iridescent glints.
• EXAMPLE 40 The following hair-setting lotion composition is prepared:
• Example 8 Vinyl acetate-crotonlc acid copolymer (vinyl acetate 90%, crotonic acid a 10%. molecular weight 45,000 to 50,000) Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. Triethanolamine, q.s.p. pH 7 This hair-setting lotion when applied to bleached hair imparts thereto an intense gray blue shade.
• This dye composition when applied to 95% naturally white hair, for 15 minutes at ambient temperature, imparts thereto, after rinsing and shampooing, a coppery blond shade.
• Dye of Example 11 0.1 g Ethyl alcohol, 96 titer 20 g Water, q.s.p. 100 g Ammonia, at 22 Be. q,s.p. pH 10 This dye composition when applied to naturally white hair for 20 minutes at ambient temperature, imparts, after rinsing and shampooing, a silvery gray shade.
• This hair-setting lotion when applied to bleached hair, imparts thereto an intense pearly pink shade.
• This dye composition when applied to 95% naturally white hair for 25 minutes at 35, imparts thereto after rinsing and shampooing a light pearly green shade.
• This dye composition when applied to 95% naturally white hair for minutes at ambient temperature, imparts thereto after rinsing and shampooing, a luminous beige with light pink glints.
• Example 15 Dye of Example 15 0.05 g Vinyl acetate-crotonic acid copolymer (vinyl acetate 90%, crotonic acid 10%, molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. I00 g Triethanolamine, q.s.p. pH 5.5
• This hair-setting lotion when applied to bleached hair imparts thereto, a very luminous, pearly blue green shade.
• Triethanolamine q.s.p. pH 7 This hair-setting lotion when applied to bleached hair imparts thereto, a bluish silvery gray shade.
• EXAMPLE 54 The following hair-setting lotion is prepared:
• EXAMPLE 56 The following hair-setting lotion is prepared:
• Dye according to Example l9 0.4 g Ethyl alcohol, 96 titer 40 g Water, q.s.p. 100 g Ammonia, at 22Be, q.s.p. pH l0 This dye composition when applied to 95% naturally white hair for 20 minutes at ambient temperature, imparts thereto after rinsing and shampooing, a silvery gray shade with rose glints.
• Triethanolamine q.s.p. pH 7 This hair-setting lotion when applied to bleached 10 hair, imparts thereto a pearly pale green shade.
• This dye composition when applied to 95% naturally white hair for 15 minutes at ambient temperature, imparts thereto, after rinsing and shampooing, a silvery gray shade with violet glints.
• the pH is equal to 7.
• This dye composition when applied to 60% naturally white hair, for 20 minutes at ambient temperature, imparts thereto, after rinsing and shampooing, a deep purplish violet shade.
• Triethanolamine q.s.p. pH 7 This hair-setting lotion when applied to bleached hair, imparts thereto, a very luminous mauve shade.
• This dye composition when applied to 95% naturally white hair, for 10 minutes at ambient temperature, imparts thereto, after rinsing and shampooing, a pearly rose beige shade.
• Dye of Example 23 Water q.s.p. Ammonia at 10%, q.s.p. pH 10 Thisdye composition when applied to bleached hair for 10 minutes at ambient temperature, imparts thereto, after rinsing and shampooing, a very luminous pale rose blond shade.
• EXAMPLE 65 The following hair-setting lotion is prepared:
• Example 25 0.05 g Vinyl acetate-crotonic acid copolymer (vinyl acetate crotonic acid 10%, molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p, 100 g Triethanolaminc, q.s.p. pH 7 This hair-setting when applied to bleached hair, imparts thereto, a rose shade with golden glints.
• This dye composition when applied to white hair, for 20 minutes at ambient temperature, imparts thereto, after rinsing and shampooing, a very luminous golden blond shade with rose glints.
• Example 26 0.15 g Vinyl acetate-crotonic acid copolymer (vinyl acetate 90%, crotonic acid 10%, molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. I00 g Triethanolamine, q.s.p. pH 7 This hairsetting lotion when applied to bleached hair, imparts thereto, a pearly pale almond green shade.
• Triethanolamine q.s.p. pH 7 This hair setting lotion when applied to bleached hair, imparts thereto, a rose shade with golden glints.
• Example 29 Dye of Example 29 0.005 g Vinyl acetate-crotonic acid copolymer (vinyl acetate 90%, crotonic acid molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. 100 g Triethanolamine, q.s.p. pH 7 This hair-setting lotion when applied to bleached hair imparts thereto, a light blond shade that is slightly rose.
• EXAMPLE 70 The following hair-setting lotion is prepared:
• Dye of Example 30 0.05 g Crotonic acid-vinyl acetate copolymer (vinyl acetate 90%, crotonic acid 10%, molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. 100 g Tricthanolamine, q.s.p. pH 7 This hair-setting lotion when applied to bleached hair imparts thereto, a violet rose shade.
• Vinyl acetate-crotonic acid copolymer (vinyl acetate 90%, crotonic acid 10%, molecular weight, 45,000 50,000)
• Triethanolamine q.s.p. pH 7 This hair-setting lotion when applied to bleached hair, imparts thereto, a strongly silvered, pale blue shade.
• Dye of Example 22 0.05 g Ethyl alcohol, 96 titer 25 g Water, q.s.p. 100 g
• the pH of the dye composition is equal to 7.
• This dye composition when applied to bleached hair imparts thereto, after a minute contact period and after rinsing and shampooing, a slightly mauve silvery gray shade.
• Dye of Example 22 0.1 g Ethyl alcohol, 96 titer 20 g Water, q.s.p. 100 g 10% lactic acid, q.s.p. pH 5 This dye composition when appliedto 95% naturally white hair, imparts thereto, after a 10 minute contact period and after rinsing and shampooing, a pearly beige gray shade.
• Example 27 0.03 g Vinyl acetate-crotonic acid copolymer (vinyl acetate crotonic acid 10%, molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. 100 g Triethanolamine, q.s.p. pH 7 This hair-setting lotion when applied to bleached hair, imparts thereto, a very luminous green blue shade.
• EXAMPLE 75 The following hair-setting lotion is prepared:
• Example 24 0.05 g Vinyl acetate-crotonic acid copolymer (as in Example 74) 2 g Ethyl alcohol, 96" titer, q.s.p. 50 Water, q.s.p. 100 g Triethanolamine, q.s.p. pH 7 This hair-setting lotion when applied to bleached hair, imparts thereto, a pearly green blue shade.
• Dye of Example 29 0.15 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. 100 g Ammonia, at 22 Be, q.s.p. pH 10 This dye composition when applied for 20 minutes to naturally white hair, imparts thereto, after rinsing and shampooing a violet shade.
• Dye of Example 19 0.2 g N-[(4'-hydroxy) phenyl]-2,6-dimethyl benzoquinone imine 0.1 g Ethyl alcohol, 96 titer 25 g Water, q.s.p. 100 g Ammonia, at 22 Be, q.s.p. pH 10 This dye composition when applied for 20 minutes to 95% naturally white hair, imparts thereto, after rinsing and shampooing, an ash dark gray shade with violet glints.
• Dye of Example 25 0.05 g N-l(4'-dimethylamino) phenyl]-2,5-dimethyl benzoquinoneimine 0.05 g Vinyl acetate-crotonic acid copolymer (vinyl acetate 90%, crotonic acid 10%. molecular weight, 45,000 50,000) 2 g Ethyl alcohol, 96 titer, q.s.p. 50 Water, q.s.p. 100 g Triethanolamine, q.s.p. pH 7 This hair-setting lotion when applied to bleached hair, imparts thereto, a silvery mauve shade.
• a dye composition for keratinous fibers comprising an aqueous solution of an indoaniline selected from the group consisting of a. an indoaniline having the formula R 2 R R R6 R7 R3 Ru wherein R R R and R each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-6 carbon atoms and halogen with the proviso that l-2 of R R R and R are other than hydrogen; R R and R each independently represent a member selected from the group consisting of hydrogen, lower alkyl having l-6 carbon atoms and lower alkoxy having l-6 carbon atoms; R represents a member selected from the group consisting of hydrogen and lower alkyl having l-6 carbon atoms; R represents a member selected from the group consisting of hydrogen and lower alkyl having l-6 carbon atoms and together with R and the nitrogen atom to which R is attached form dihiydro-oxazine; and Z represents a member selected from the group
• the dye composition of claim 1 having a pH ranging between 4 11.
• the dye composition of claim 1 which also contains a low molecular weight alkanol present in amounts of 20 weight percent of said composition.
• the dye composition of claim 1 which also includes a glycol selected from the: group consisting of propylene glycol and butyl glycol present in amounts of l-6 weight percent of said composition.
• the dye composition of claim 1 also including a dye selected from the group consisting of a nitrobenzene dye, an indophenoland an indoaniline other than that defined in claim 1.
• a process of dyeing keratinous fibers comprising impregnating said fibers to be dyed with the composition of claim 1 in amounts effective to dye said keratinous fibers, permitting said composition to remain in contact with said fibers for a period ranging from about 3 to 30 minutes, rinsing said fibers and drying said fibets.
• the aqueous solution comprises an aqueous solution of a lower alkanol selected from the group consisting of ethanol and isopropanol present in amounts of about 20 to 70 percent by weight of said composition
• said composition also includes l-3 percent by weight of a film forming resin selected from the group consisting of pol yvinylpyrrolidone having a molecular weight of 10,000-400,000, copolymer of 10% crotonic acid and vinyl acetate having a molecular weight ranging from 10,000 to 70,000 and a copolymer of vinylpyrrolidone and vinyl acetate having a molecular weight ranging from about 30,000 to 200,000 wherein the ratio of VP to VA ranges between 50-70150-30, and (3) said indoaniline is present in amounts of about 0.002 to 1 percent by weight of said composition.

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Citations (6)

• 1971
  • 1971-12-29 GB GB6052371A patent/GB1338950A/en not_active Expired
  • 1971-12-29 BE BE777464A patent/BE777464A/xx unknown
  • 1971-12-29 ES ES398433A patent/ES398433A1/es not_active Expired
  • 1971-12-29 AT AT1121571A patent/AT316758B/de not_active IP Right Cessation
  • 1971-12-29 CH CH1912871A patent/CH536630A/fr not_active IP Right Cessation
  • 1971-12-29 US US213750A patent/US3867094A/en not_active Expired - Lifetime
  • 1971-12-29 AR AR239878A patent/AR192336A1/es active
  • 1971-12-29 FR FR7147372A patent/FR2121101A5/fr not_active Expired
  • 1971-12-29 DE DE19712165463 patent/DE2165463A1/de active Pending
  • 1971-12-29 IT IT71269/71A patent/IT996554B/it active
  • 1971-12-29 SE SE7116841A patent/SE383737B/xx unknown
  • 1971-12-29 NL NL7118019A patent/NL7118019A/xx unknown
  • 1971-12-29 CA CA131,345A patent/CA1005444A/fr not_active Expired
  • 1971-12-30 AU AU37416/71A patent/AU459336B2/en not_active Expired
• 1974
  • 1974-05-21 ES ES426551A patent/ES426551A1/es not_active Expired

Patent Citations (6)

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